Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Detalhes bibliográficos
Autor(a) principal: Raposo, M. Manuela M.
Data de Publicação: 2005
Outros Autores: Sousa, Ana M. R. C., Kirsch, G., Ferreira, F., Belsley, M., Gomes, E. Matos, Fonseca, A. Maurício C.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/7846
Resumo: Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.
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spelling Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical propertiesPyrrolesThiophenesDonor-acceptor thienylpyrrolesTricyanovinylationChromophoresSolvatochromismElectrochemistryHyper-Rayleigh scattering (HRS)Non-linear optical (NLO) materialchromephoresScience & TechnologyTricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.Fundação para a Ciência e Tecnologia (FCT) - POCTI, FEDER (ref.POCTI/QUI/37816/2001).ElsevierUniversidade do MinhoRaposo, M. Manuela M.Sousa, Ana M. R. C.Kirsch, G.Ferreira, F.Belsley, M.Gomes, E. MatosFonseca, A. Maurício C.20052005-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/7846eng"Tetrahedron". ISSN 0040-4020. 61:50 (Dec. 2005) 11991-11998.0040-402010.1016/j.tet.2005.09.062http://www.sciencedirect.com/science/journal/00404020info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:40:09Zoai:repositorium.sdum.uminho.pt:1822/7846Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:36:54.236906Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
title Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
spellingShingle Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
Raposo, M. Manuela M.
Pyrroles
Thiophenes
Donor-acceptor thienylpyrroles
Tricyanovinylation
Chromophores
Solvatochromism
Electrochemistry
Hyper-Rayleigh scattering (HRS)
Non-linear optical (NLO) material
chromephores
Science & Technology
title_short Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
title_full Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
title_fullStr Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
title_full_unstemmed Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
title_sort Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
author Raposo, M. Manuela M.
author_facet Raposo, M. Manuela M.
Sousa, Ana M. R. C.
Kirsch, G.
Ferreira, F.
Belsley, M.
Gomes, E. Matos
Fonseca, A. Maurício C.
author_role author
author2 Sousa, Ana M. R. C.
Kirsch, G.
Ferreira, F.
Belsley, M.
Gomes, E. Matos
Fonseca, A. Maurício C.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Raposo, M. Manuela M.
Sousa, Ana M. R. C.
Kirsch, G.
Ferreira, F.
Belsley, M.
Gomes, E. Matos
Fonseca, A. Maurício C.
dc.subject.por.fl_str_mv Pyrroles
Thiophenes
Donor-acceptor thienylpyrroles
Tricyanovinylation
Chromophores
Solvatochromism
Electrochemistry
Hyper-Rayleigh scattering (HRS)
Non-linear optical (NLO) material
chromephores
Science & Technology
topic Pyrroles
Thiophenes
Donor-acceptor thienylpyrroles
Tricyanovinylation
Chromophores
Solvatochromism
Electrochemistry
Hyper-Rayleigh scattering (HRS)
Non-linear optical (NLO) material
chromephores
Science & Technology
description Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.
publishDate 2005
dc.date.none.fl_str_mv 2005
2005-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/7846
url http://hdl.handle.net/1822/7846
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Tetrahedron". ISSN 0040-4020. 61:50 (Dec. 2005) 11991-11998.
0040-4020
10.1016/j.tet.2005.09.062
http://www.sciencedirect.com/science/journal/00404020
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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